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Crystal forms of 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine

a technology of methylethylamino and methylethyl, which is applied in the field of 15methanesulfonate salts, can solve the problem of not having a reliable method to predict the crystal structure of a given drug, and achieve the effect of accurate determination

Inactive Publication Date: 2002-09-17
PHARMACIA & UPJOHN CO +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The exact dosage and frequency of administration depends on the particular condition being treated, the severity of the condition being treated, the age, weight, general physical condition of the particular patient, other medication the individual may be taking as is well known to those skilled in the art and can be more accurately determined by measuring the blood level or concentration of CD4 in the patient's blood and / or the patient's clinical response.

Problems solved by technology

It is important to note that there is no reliable method to predict the observable crystal structures of a given drug or to predict the existence of polymorphs with desirable physical properties.

Method used

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  • Crystal forms of 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine

Examples

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Effect test

example 1

"S" Crystal Form Of 1-[5-methanesulfonamidoindolyl-2-carbon-yl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine Monomethanesulfonate Salt From A Different Crystal Form

1-[5-Methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]-piperazine monomethanesulfonate salt (crystal form XI, 25 g) is dissolved in methanol (125 ml) by refluxing. The mixture is concentrated atmospherically to a volume of 40-45 ml. While maintaining reflux, warm acetone (100 ml) is added over 5 min. The mixture is held at reflux and crystals are observed within 30 min. The slurry is stirred at reflux for a total of 60 min and then filtered. The filter cake is washed with acetone (100 ml) and dried to give the title compound, mp 228-232.degree..

example 2

"S" Crystal Form Of 1-[5-methanesulfonamidoindolyl-2-carbon-yl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine Monomethanesulfonate Salt From The Free Base

1-[5-Methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]-piperazine (THF solvate, 100 g, 0.18 moles) is slurried in methanol to which is added methanesulfonic acid (19.6 g, 0.20 moles). The mixture is warmed to 40.degree. and isopropanol (325 ml) is added. The mixture is held at 37-42.degree. and crystals are observed within 2-3 hours. The slurry is cooled over 2 hr to 150 and filtered. The cake is washed with isopropanol (100 ml) and methyl-t-butyl ether (250 ml) then dried to give the title compound, mp 221-228.degree..

example 3

"S" Crystal Form Of 1-[5-methanesulfonamidoindolyl-2-carbon-yl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine Monomethanesulfonate Ssalt From The Free Base

1-[5-Methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]-piperazine (THF solvate, 6.58 kg, 12.77 moles) in methanol (50 l) and methylene chloride (150 l) is filtered through a 0.6 micron filter, then rinsed with methylene chloride (50 l). The mixture is concentrated under reduced pressure at 10.degree. to 10 l, diluted with acetonitrile (160 kg) and concentrated to 10 l. The residue is then slurried in acetonitrile (240 l), the mixture is heated to 63.degree. and methanesulfonic acid (1.29 kg, 13.4 moles) is added. The mixture is heated further to 70-75.degree. and after stirring at that temperature for 4.5 hr it is cooled to 32.degree.. The product is collected on a filter, rinsed with acetonitrile (50 l) and dried to give the title compound, mp 222-229.degree..

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Abstract

The present invention relates to two novel crystal forms of a known compound, 1-[5-Methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl] piperazine monomethanesulfonate salt, which are useful for treating humans who are HIV positive, which are identified by a powder X-ray diffraction spectrum known commonly as the "S" and "T" forms.

Description

1. Field of the InventionThe field of the invention is crystal forms of a known compound, 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethyl-amino)-2-pyridinyl]piperazine monomethanesulfonate salt, which is a pharmaceutical useful in treating individuals who are HIV positive.2. Description of the Related ArtIt is known to those skilled in the art that solids including pharmaceuticals often have more than one crystal form and this is known as polymorphism. Numerous examples are cited in the standard references of solid state properties of pharmaceuticals, Byrn, S. R., Solid-State Chemistry of Drugs, New Your, Academ. Press (1982); Kuhnert-Brandstatter, M., Thermomiscroscopy In The Analysis of Pharmaceuticals, New York, Pergamon Press (1971) and J. Pharm. Sci., 58, 911 (1969). Byrn states that, in general, polymorphs exhibit different physical characteristics including solubility and physical and chemical stability. It is important to note that there is no reliable method ...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07D401/12C07D401/00A61K31/495A61K31/496A61P31/12A61P31/18A61P37/04
CPCC07D401/12A61P31/12A61P31/18A61P37/04
Inventor HAVENS, JEFFREY L.SMITH, DONALD P.BERGREN, MICHAEL S.LYSTER, MARK A.
Owner PHARMACIA & UPJOHN CO
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